Holiday rentals in Elkton

Guest house in St. Augustine

4.99 out of 5 average rating, 377 reviews

Pelican Guesthouse-Spacious/Quiet/Comfortable

Quiet, spacious guesthouse. Comfortable beds and immaculately kept. Read our reviews :) A few miles from gorgeous beaches, historic downtown and St Augustine Amphitheater. Friendly neighborhood, accessible to beautiful walks along the Matanza River. Public park and playground at the end of the street. Self check in, private entrance, flat screened TV's, full kitchen. Thoughtful decor and local artwork to enjoy. Full laundry room and off street parking for two car. Strictly a pet-free listing.

4.97 out of 5 average rating, 408 reviews

Genovar Mansion Rose Garden Suite Private Entrance

The direct view of a gorgeous live oak canopy on Magnoila Avenue and incredible architecture make this historic home a memorable place to stay. This romantic ground floor suite is perfect for couples with a private entrance, queen poster bed, living room, spacious bathroom, individual climate control, heirloom antiques and reserved driveway parking spot. The home is located within the historic district, close to trolley stops and within easy walking distance to downtown. 6 minutes to the beach.

5 out of 5 average rating, 38 reviews

Flat in St. Augustine

Peach Room- studio apartment 15 min to beaches

No ridiculous 'cleaning fees.' New studio apartment *attached to main home* 15 minutes from area beaches. Ideal for solo travelers but suitable for couples. Quiet residential neighborhood with lakeside walking trails. Private entrance. Private bathroom. Queen bed. Kitchen. Fast wifi. 1 Parking space. Outdoor patio. Minifridge, TV, microwave, Keurig, air-fryer. Everything needed for a comfortable stay, 15 minutes from area beaches, St Augustine Amphitheater, Anastasia State Park or downtown.

4.98 out of 5 average rating, 336 reviews

Cozy studio 15 min to beaches & historic downtown

Outstanding location & amenities, 15 minutes to beaches & historic downtown, minutes walk to the intercostal w/ piers, boat ramps, gorgeous for pleasant walks w/ swings & benches. Close to plenty of shopping/dining. Quiet, friendly neighborhood w/ ample parking-trailers & boats welcome. Kid friendly w/ toys, pack + play & more. Laundry, walk-in shower, private entrance. Private deck w/ cheerful seating. Well equipped kitchenette. Happy to accommodate special requests! Easy drive to theme parks!

4.98 out of 5 average rating, 481 reviews

Winter Hawk Hideout

15 minutes from ol' St Augui. Located in the heart of this typical Florida woods and nested by oaks that saw the Seminole War as we are walking distance from Ft Peyton and 2 miles away from where Osceola was captured. The house sits on half acre of gardens and the decor is ranch, asian and whimsical .The goal is for you to feel transported away for a while. I do have 2 very small, well behaved and quiet dogs and one never seen cat. They do not have access to your quarters or are allowed in.

4.97 out of 5 average rating, 140 reviews

MarshMellow-Island Guest Suite Beach Amphitheater

Your own cozy guest suite with private entry. Lovely little bedroom and beautiful bathroom . Private porch and sitting area. Located adjacent our guest studio but the suite is entirely yours and private. These two share a lush garden path, but have separate porches and entrances. The MarshMellow is a well thought out accommodation that has everything we think you'll need for a lovely stay in St. Augustine. A 20 minute stroll to the Amp and short drive or bike to the beaches or downtown.

4.9 out of 5 average rating, 153 reviews

St. Aug cottage, great location!

Newly updated tropical cottage close to everything in St. Augustine and steps from the Matanzas River boat ramp. This 2 bedroom, 2 bath home has wood and tile floors and a lovely screened patio to relax looking at nature and listening to the bubbling fountain. Back yard is fully fenced. 3 miles to downtown, beaches, alligator farm, or the amphitheater. Beautiful area for walking along the Matanzas river and your well loved and cared for pets are always welcome. Boat parking available.

4.9 out of 5 average rating, 107 reviews

Mermaid relaxing studio. King bed. Pool.

Dear Guests, let us introduce our "Mermaid Relaxing" studio! KING BED! This studio is a private, compact, above-garage guest suite, with a private entrance upstairs from the (shared with our family) backyard. The Mermaid suite is ideal for a couple and features a King bed! Guests have own sitting area on the deck and are welcome to share the underground pool with us. Easy, ample free parking. Breathtaking pine forest outdoor views. Free wi-fi, Netflix, and Hulu apps on smart TV are included!

Tiny home in St. Augustine

4.97 out of 5 average rating, 271 reviews

Enjoy St. Aug's Best Tiny House

Creekside Cottage is a tiny house guest apartment. It's a great choice for couples or solo travelers looking for simple, stylish, and unique accommodations. The home is located across the street from Moultrie Creek which offers beautiful views. The neighborhood is a quiet, safe, residential area within a 10-15 minute drive to downtown St. Augustine or the beach. You'll have privacy, parking, and a beautiful garden space to enjoy during your stay. The Cottage offers wifi and Keurig coffee.

4.94 out of 5 average rating, 66 reviews

Farm stay in Elkton

Farm stay in private MIL suite near StAug

Experience your dream getaway on the farm! Our spacious suite with attached patio looks over a gorgeous pool, and beyond that you can see peacocks, chickens and turkeys free ranging across 11 beautiful acres. Lounge by the pool, take in the breath taking evening skies, and relax with view of animals far off in the background. Hang by the fire pit, take a walk to visit the goats, donkeys, emus, alpacas, or go for a stroll down the beautiful oak lined roads nearby. The views are stellar.

4.87 out of 5 average rating, 103 reviews

3 BR Modern Space, 5 min to Downtown

This 3 bedroom sanctuary on Stewart Street is a dog-friendly, modern home only 3 miles from downtown with a large fenced-in yard, firepit & central AC. Enjoy this serene space after a day spent exploring the city center, dining out at wonderful restaurants, or lounging on nearby beaches. It is located in a quiet cul-de-sac and has family-friendly amenities for children and fur-babies alike. You will love the large fenced yard, outdoor dining, the welcoming patio, and no pet fees!